Highly regioselective synthesis of undecylenic acid esters of purine nucleosides catalyzed by Candida antarctica lipase B

Biotechnology Letters

Volumn 33, Issue 11, 2011, Pages 2233-2240

  Gao, Wen Li ^a   Li, Ning ^a   Zong, Min Hua ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Acylation; Enzyme substrate recognition; Lipase; Nucleosides; Undecylenic acid vinyl ester

Indexed keywords

CANDIDA ANTARCTICA LIPASE B; ENZYMATIC ACYLATION; ENZYME DOSAGE; ENZYME SUBSTRATE RECOGNITION; ESTER DERIVATIVES; INITIAL ACTIVITY; MODEL REACTANT; MOLAR RATIO; NUCLEOSIDES; OPERATIONAL STABILITY; OPTIMUM CONDITIONS; PRODRUGS; REACTION TEMPERATURE; REGIO-SELECTIVE; REGIOSELECTIVE SYNTHESIS; UNDECYLENIC ACID; VINYL ESTERS;

ACYLATION; BIOMOLECULES; CANDIDA; ENZYMES; ESTERIFICATION; ESTERS; ISOMERS; LIPASES; MOLECULAR SIEVES; ORGANIC SOLVENTS; REACTION RATES; SYNTHESIS (CHEMICAL); YEAST;

REGIOSELECTIVITY;

10 UNDECENOIC ACID; ESTER; LIPASE B, CANDIDA ANTARCTICA; PURINE NUCLEOSIDE; SOLVENT; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; CHEMISTRY; ENZYME SPECIFICITY; ENZYME STABILITY; ENZYMOLOGY; METABOLISM; STEREOISOMERISM; TEMPERATURE;

CANDIDA; ENZYME STABILITY; ESTERS; LIPASE; PURINE NUCLEOSIDES; SOLVENTS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TEMPERATURE; UNDECYLENIC ACIDS;

CANDIDA ANTARCTICA;

EID: 80053201257     PISSN: 01415492     EISSN: 15736776     Source Type: Journal    
DOI: 10.1007/s10529-011-0685-6     Document Type: Article

References (26)

1. De Clercq E, Field HJ (2006) Antiviral prodrugs-the development of successful prodrug strategies for antiviral chemotherapy. Br J Pharmacol 147: 1-11.
2. Diaz-Rodriguez A, Fernandez S, Lavandera I, Ferrero M, Gotor V (2005) Novel and efficient regioselective enzymatic approach to 3′-, 5′- and 3′, 5′-di-O-crotonyl 2′-deoxynucleoside derivatives. Tetrahedron Lett 46: 5835-5838.
3. Ferrero M, Gotor V (2000) Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. Chem Rev 100: 4319-4347.
4. Galmarini CM, Mackey JR, Dumontet C (2002) Nucleoside analogues and nucleobases in cancer treatment. Lancet Oncol 3: 415-424.
5. Garcia J, Fernandez S, Ferrero M, Sanghvi YS, Gotor V (2003) Novel enzymatic synthesis of levulinyl protected nucleosides useful for solution phase synthesis of oligonucleotides. Tetrahedron Asymmetry 14: 3533-3540.
6. Lavandera I, Fernandez S, Magdalena J, Ferrero M, Kazlauskas RJ, Gotor V (2005) An inverse substrate orientation for the regioselective acylation of 3′, 5′-diaminonucleosides catalyzed by Candidaantarctica lipase B? ChemBioChem 6: 1381-1390.
7. Li XF, Zong MH, Wu H, Lou WY (2006) Markedly improving Novozym 435-mediated regioselective acylation of 1-β-D-arabinofuranosylcytosine by using co-solvent mixtures as the reaction media. J Biotechnol 124: 552-560.
8. Li N, Zong MH, Liu XM, Ma D (2007) Regioselective synthesis of 3′-O-caproyl-floxuridine catalyzed by Pseudomonas cepacia lipase. J Mol Catal B 47: 6-12.
9. Li N, Ma D, Zong MH (2008a) Enhancing the activity and regioselectivity of lipases for 3′-benzoylation of floxuridine and its analogs by using ionic liquid-containing systems. J Biotechnol 133: 103-109.
10. Li N, Zong MH, Ma D (2008b) Regioselective acylation of nucleosides catalyzed by Candida antarctica lipase B: enzyme substrate recognition. Eur J Org Chem 5375-5378.
11. Li X, Wu Q, Zhang F, Lin XF (2008c) Chemoenzymatic synthesis, characterization, and controlled release of functional polymeric prodrugs with acyclovir as pendant. J Appl Polym Sci 108: 431-437.
12. Li N, Zeng QM, Zong MH (2009a) Substrate specificity of lipase from Burkholderia cepacia in the synthesis of 3′-arylaliphatic acid esters of floxuridine. J Biotechnol 142: 267-270.
13. Li N, Zong MH, Ma D (2009b) Regioselective acylation of nucleosides and their analogs catalyzed by Pseudomonas cepacia lipase: enzyme substrate recognition. Tetrahedron 65: 1063-1068.
14. Li N, Zong MH, Ma D (2009c) Thermomyces lanuginosus lipase-catalyzed regioselective acylation of nucleosides: Enzyme substrate recognition. J Biotechnol 140: 250-253.
15. Li N, Smith TJ, Zong MH (2010) Biocatalytic transformation of nucleoside derivatives. Biotechnol Adv 28: 348-366.
16. Mak KH, Yu CY, Kuan IC, Lee SL (2009) Immobilization of Pseudomonas cepacia lipase onto magnetic nanoparticles for biodiesel production. ISESCO Sci Technol Vision 5: 19-23.
17. Pleiss J, Fischer M, Schmid RD (1998) Anatomy of lipase binding sites: the scissile fatty acid binding site. Chem Phys Lipids 93: 67-80.
18. Plunkett W, Gandhi V (2001) Purine and pyrimidine nucleoside analogs. In: Giaccone G, Schilsky R, Sondel P (eds) Cancer chemotherapy and biological response modifiers: annual 19. Elsevier Science, Amsterdam, pp 21-46.
19. Raku T, Kitagawa M, Shimakawa H, Tokiwa Y (2003) Enzymatic synthesis of hydrophilic undecylenic acid sugar esters and their biodegradability. Biotechnol Lett 25: 161-166.
20. Simeo Y, Sinisterra JV, Alcantara AR (2009) Regioselective enzymatic acylation of pharmacologically interesting nucleosides in 2-methyltetrahydrofuran, a greener substitute for THF. Green Chem 11: 855-862.
21. Tokiwa Y, Kitagawa M, Raku T (2007a) Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase. Biotechnol Lett 29: 481-486.
22. Tokiwa Y, Kitagawa M, Raku T, Yanagitani S, Yoshino K (2007b) Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on melanin synthesis. Bioorg Med Chem Lett 17: 3105-3108.
23. van der Steen M, Stevens CV (2009) Undecylenic acid: a valuable and physiologically active renewable building block from castor oil. ChemSusChem 2: 692-713.
24. Wang ZY, Li N, Zong MH (2009) A simple procedure for the synthesis of potential 6-azauridine prodrugs by Thermomyces lanuginosus lipase. J Mol Catal B 59: 212-219.
25. Weber HK, Weber H, Kazlauskas RJ (1999) 'Watching' lipase-catalyzed acylations using 1H NMR: competing hydrolysis of vinyl acetate in dry organic solvents. Tetrahedron Asymmetry 10: 2635-2638.
26. Zhao ZL, Zong MH, Li N (2009) Efficient regioselective synthesis of 3′-O-crotonyl-floxuridine catalyzed by Pseudomonas cepacia lipase. Biotechnol Appl Biochem 52: 45-51.